Boron tribromide → HCID 69217960, compound

HRID 272718Notes

Reaction equation

HRID 272718 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[CH:14][C:15]([O:17]CC)=[CH:16][C:8]=3[NH:7][C:6]=2[CH:20]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:8]=3[NH:7][C:6]=2[CH:20]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69217075HCID 69217075, compound

Product 1

HCID 69217960HCID 69217960, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of Example 506C (1.87 g, 6.5 mmol) in dichloromethane (50 mL) at −78° C. was treated dropwise with a 1.0M solution of BBr3 in dichloromethane, stirred overnight and allowed to reach room temperature, quenched with a saturated solution of ammonium chloride, concentrated under vacuum, and extracted with ethyl acetate. The extracts were combined, washed with brine, dried (MgSO4), filtered, and concentrated under vacuum to provide the desired product.

Workup

  1. customto reach room temperature
  2. customquenched with a saturated solution of ammonium chloride
  3. concentrationconcentrated under vacuum
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0af92a2122354ca59371cc540d329782
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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